


Initiation

by morlawny



Category: Red Dead Redemption
Genre: Alternate Universe, Explicit Sexual Content, Female Reader, Gangbang, Gangbang Initiation, Gratuitous Smut, Multi, Plot What Plot/Porn Without Plot, who doesn't love a good gangbang
Language: English
Status: In-Progress
Published: 2019-01-22
Updated: 2019-05-25
Packaged: 2019-10-11 10:26:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 5,162
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17445140
Author URL: https://archiveofourown.org/users/morlawny/pseuds/morlawny
Summary: The gang of Dutch van der Linde is the most notorious in all of the southern states; mostly for their way of initiating new members.Most chapters will be posted as the writers finish them. It is a very large WIP, so we apologize for any inconvenience. We agreed that posting chapters as they're completed is the best way to go about such a large project, that way you all can enjoy the content as we work on more.This work contains chapters for all gang members and a female reader. Credit to the writer of each character will be in their respective chapters.





	1. Arthur Morgan

**Summary for the Chapter:**

> Our prospective reader gets a taste of Arthur Morgan.
> 
> Written by myself.

You had to keep reminding yourself that you wanted this. You knew the price of becoming a member of the Van Der Linde gang, and you had prepared yourself. After just a few rounds, however, you were starting to doubt yourself.

You laid in Arthur's cot now, breathing heavily as you tried not to move. Charles had graciously carried you over after his turn had ended with you and made sure you were okay before going to get Arthur.

The pace of your heartbeat started to accelerate as you saw the flap of the canvas move, and the tall, handsome figure of Arthur Morgan moved closer to you. You couldn't quite catch his expression, but you could tell he was willing to wait until you had at least recovered a little bit.

He sat down next to you on the cot, and you could see his face a lot clearer now as the light from the oil lamp illuminated his features. His strong jawline, the stubble on his face, and those hazel eyes... God damn those eyes.

Your breath caught, and he noticed. A small smile came over him and he reached forward, brushing some hair out of your face. You knew for a fact that you didn't have to worry about him being rough. The man exudes sex, but for some reason, you felt safe with him. And that was all you wanted right now.

"You don't gotta worry, I'll take good care of ya," he told you with that deep southern drawl, stroking your cheek with his thumb.

A blush flushed your face and you could have sworn your heart skipped a beat. This man was utter perfection, and he hadn't even started yet.

"Tell me if you want me to stop, okay?"

You gave a silent nod, closing your eyes and tilting your head back as you felt Arthur close the distance between you both, placing his lips on your neck and kissing down toward your covered chest. He pulled back the thin robe on both sides and continued down stopping between your breasts.

His left hand reached up to grab your hip, then slowly made its way up your waist to rest right beneath your shoulder blade, keeping your body close. A soft, breathy sigh of pleasure escaped your lips as his own traveled slowly back up your chest and neck, causing your skin to prickle. 

He stopped next to your ear, and spoke softly in a voice that made you shudder with anticipation, "Let's see how ready you are..."

His other hand slid slowly down your stomach, past your hips and along your inner thigh, and his sigh right next to your ear made you shiver as he felt the heat between your legs. 

Arthur's middle finger gently slid along your slick opening, and you released an impatient, breathless sigh as you tilted your hips up toward his fingers. A light chuckle accompanied his next words,

"Just can't wait, can ya? Well... I reckon you've waited long enough."

With that, he pushed his finger in with ease, and your eyes flew open at the sudden feeling. It wasn't a bad feeling, no- it was the opposite. You found yourself wanting more, not just his fingers. Surely you were wet enough to handle his cock now, right?

Arthur didn't seem to agree, however. He pulled his head back a bit to look at you while his fingers continued their assault. Another finger joined the first, and you couldn't suppress the moan that escaped you as he stretched you open with them. Your mouth fell open and you arched into him, your fingers curling into the blankets on the cot as you tried to contain yourself.

"Don't hold back on me now, darlin'... I wanna hear you," Arthur murmured, continuing to work his fingers in and out. His assault was slow and teasing, and it felt so goddamn good.

A moan escaped your throat as the blond found the spot he'd been looking for. A wry smile crossed his features as he committed the spot to memory, and then stopped, moving both of his hands to his belt buckle. It was time, and God were you ready for it.

You watched with rapt attention as he stood up and worked to unbuckle and pull down his trousers, and you couldn't help but be drawn to the very obvious, surprisingly large bulge that swelled underneath. Your breath stuttered as you imagined him thrusting into you, and he couldn't help but chuckle at your expression.

"You know what you want, that's for sure."

He stepped closer to you and pulled his trousers down just past his ass, and took his cock in his hand, giving it a slow, languid stroke as his eyes locked on your body. The look on his face alone was nearly enough to push you over the edge.

Your legs spread instinctively and voluntarily as he positioned himself over you, not taking his eyes off of yours. Your heart was racing a mile a minute, but you were absolutely ready for this.

He positioned his cock at your entrance, letting out a soft growl as he moved it along the slick opening. You arched into it, about to let out a whine; but you were quickly cut off as he thrust into you, causing your mouth to drop.

"Oh, sh-" Was all you could gasp out as he filled you completely, stretching you open so perfectly that you could probably cry.

Arthur's expression turned hungry as he watched your reactions. Even that was sexy, the way his eyes roamed up and down your body as he buried himself to the hilt. A soft moan escaped your throat as he did. He placed a hand on your left thigh and hiked it up toward his waist, digging his fingers into the soft skin before starting to thrust back and forth slowly. He did this for a long moment, taking it all in.

"You feel mighty fine, sweetheart," he said softly, his voice low enough to make you shiver even as heat took over your entire form. He continued the slow pace for a while, and you couldn't help but feel grateful for it. It was almost relaxing, feeling his cock slide in and out of you with such fluid movements. The wetness at your entrance certainly made it easier for you both as well.

The blonde's body shifted so that you laid on your back, but he kept his right hand on your body, while the other went to the side of your head, keeping his body up as he continued his thrusts. Every now and then he'd let out a soft grunt as he brushed against a part of you that rubbed him the right way, and along with that, the hand on your waist dug into your skin in a way that could easily push you over the edge by itself.

"Arthur..." His name came out of your mouth in a breathless moan, while your back arched sinfully as his cock brushed against a certain spot, and he let out a low moan in return, squeezing your hip.

"Gettin' real close, darlin'," he growled.

His thrusts got noticeably quicker, and you couldn't stop the cry of pleasure that escaped your throat at the sensation the friction caused. You gave a few quick nods as you managed to reply with a pleasure filled,

"M-me too."

If there was one thing you could say about Arthur, it was that he was truly a gentleman. It was clear that he wasn't going to climax until you did first, and if you were honest, you couldn't hold it back anymore, anyway. As the head of his cock brushed against that spot one last time, your entire body jerked as waves upon waves of ecstasy rolled through you.

Arthur was panting heavily at this point, and with one last thrust, he pulled out of you at the very last second and climaxed with a loud grunt. He stroked himself through it, painting your stomach and chest with hot, sticky ribbons.

He fell back on his knees once he had finished, letting out a long sigh of satisfaction. You laid where you were, panting heavily as you came down from your own climax. The hand on your hip squeezed gently one more time before letting go, and Arthur moved to stand, tucking himself away. Your gaze met his and he started to speak,

"You're doin' good, (Y/N). Don't lose faith, okay?"

A nod was all you gave in response, and he smiled at the determination in your expression. "We need more folks like you, that's for sure. You get some rest for now. I'll come get ya in a bit."

You thanked him, feeling your face flush as he tipped his head politely and left the tent, leaving you to your own devices. You released a breath you hadn't known you were holding, and ran a hand through your hair.

You could do this.


	2. Sean MacGuire

**Summary for the Chapter:**

> Sean has his turn with the new prospect.
> 
> Written by redmodernredemption from tumblr.

It was Sean’s turn, and the Irish man was already chomping at the bit. Hearing all the moans and groans and every delicious little noise had him worked up. He needed to be inside you, and now. He slid into the tent, his eyes on your naked body.

“Don’ tell me those fools already got ya worn out, lassie,” he teased, and your tired, anxious gaze met his.

“Just need a few minutes,” you murmured, and he shook his head.

“You’ll get ya rest. When ole Dutch says so. Been listin’ to ya outside, pet. And ya sound so damn good.”

He almost missed the thick swallow, and the almost anxious whimper. So similar to another they had initiated. 

It made his cock twitch in his pants, already straining against the fabric. He couldn’t stop himself from reaching and stroking your leg.

“Ya jus’ lay back an’ let me handle it,” he purred, and he could see his voice was having some effect on you. 

“Before I’m through, you’ll be beggin’ for my cock. Such a pretty little thing, aren’t ya? Bet ole Dutch and Hosea been makin’ ya feel like a goddess.”

You bit your lip, and he chuckled as he slid his hand up to your thigh. Oh, he was going to have fun with you. So much fun. But first, he needed to gauge just how sensitive you were right now. He dropped to his knees and grasped both of your legs, pulling you closer.

“Jus’ need to get a taste of ya, doll,” he muttered before diving in, his tongue quickly working it’s way inside of you. Your hands all but flew to his hair, and he could feel you both attempting to push him away and pull him further into your sex. Oh, you were sensitive alright. And he was going to exploit that for all he could.

But right now, he was enjoying how damn good you tasted.

He groaned and wriggled his tongue deeper, his eyes sliding closed. You tasted like heaven. Better than whiskey, and sweeter than moonshine. He could spend forever right there, between your legs, feeling them tremble under his hands.

He slid up to your clit, and you nearly squealed at the sensation.

“Not yet, ya don’t,” he ordered, pulling away in spite of your protest. “You’ll get ya chance. When I say so. But I plan on takin’ my sweet time with ya.”

You were already panting, so close to the edge already. And he loved it. Loved seeing you tremble after being denied. And he would deny you over and over until he heard your sweet voice begging. Though he wasn’t sure how long he’d be able to control himself. His cock was already aching, begging to be buried in your tight cunt.

“Jus’ breath, lass,” he instructed. “I got ya. Ya ain’t gotta worry.”

“Please,” you breathed, your voice shaky, and he nearly gave in right then and there. “Please, it’s too much, too… too…”

“I know, luv.” Of course, he knew. He’d done this himself, been on the receiving end of the initiation. But there were less people then, and it didn’t take nearly as long. “You jus’ focus on me. Don’ worry about them fool jus’ yet.”  
He gently stroked the inside of your thigh, then eased two fingers into you, making you moan loudly.

“That’s it. Let the whole camp know what’s happenin’. Don’ you dare try an’ keep quiet ‘bout it.” He began pumping his fingers, grinning at how your hips moved of their own accord. You were worked up, already begging, and so responsive to his voice.

And he was going to enjoy every minute.

“Look at ya. Fuckin’ yourself on my fingers. Wonder if you’ll be doin’ the same on my cock. Or are ya gonna lay back and scream as I fuck ya open, showin’ ya how a real man fucks a woman? An’ those damn tits of yours, they’re beggin’ for attention.”

And they were. His mouth watered as he watched your chest heave, the little mewls and whimpers all but urging him to nip and suckle on those pert nipples. But he’d save that for later. For when he was finally inside you, feeling you squeeze his cock, damn near milking him.

“Maybe I should take my time. Fuck ya nice an’ slow, make ya beg for more, tease ya till ya can’t seem to talk. Or maybe, just maybe, I should fuck ya thoroughly, nice an’ hard, make ya eyes roll back as you feel me inside ya.”  
Your back began to arch, and he pulled his hand away, making you whine and squirm.

“I told ya. Not yet. Not until I damn well say so.”  
He could see the tears as your eyes met his, and he gently wiped them away. You would need to rest once he was done. Otherwise, you wouldn’t survive the initiation. 

There were too many of them now, and he knew it.

Oh, but he knew you’d feel so good afterwards.

“Last time, I promise. Soon, though, you’ll be stuffed with something a lot thicker than my fingers. An’ you’ll have to fight to keep from disobeyin’ me. Understood, lass?” You nodded. “Good. You do whatever you have to do to keep from tumblin’ over that edge, but don’ ask me to stop. Cause I ain’t gonna.”

You moaned as he shoved his pants down. Too worked up to bother taking them off. He needed you. All this teasing had him feeling like an animal, and for now, you were his to fuck as he saw fit. He stroked himself a few times, trying to maintain some form of self-control.

Taking it slow was no longer an option.

“Please, Sean, please, fuck me open, let me feel your cock inside me, rubbing against me, please please please.”

Well, there went his self-control.

He lined himself up and slammed into you, groaning loudly. Your scream echoed in his ears, and it spurred him into motion, his hips pulling back and snapping into yours. The animal side of him had taken over, and all he could focus on was the warm, tight, wet flesh around his cock.

His lips found your nipple, and you weakly struggled.

“Too much,” you pleaded, only to have him pin your hands above your head.

“Told ya not to try an’ stop me,” he murmured before lavishing your nipple with his tongue, sucking and biting.

His eyes were dark with lust, but he could see you fighting the urge to just let go. He shifted the angle of his hips a bit, and the way you jolted told him everything he needed to know.

He had found the oh so elusive sweet spot, and now he was going to enjoy himself.

Each thrust was aimed for your g spot, making you scream incoherently into the night. He would swap between your nipples, biting and sucking until you were practically vibrating beneath him. He could feel himself growing close, his balls heavy and aching and full.

“Let go, lass. I won’t be far behind you.”

And let go you did. You screamed his name, clenching around him, and he growled as his cock twitched and filled you up. If he thought eating you out was heaven, then he was wrong. Feeling you beneath him, shuddering and moaning, was much, much better.

By the time he had calmed down, you had passed out. He smiled and kissed your head, then tucked himself away and slid back out of the tent.


	3. Josiah Trelawny

**Summary for the Chapter:**

> You're starting to become wary about this, but Josiah quickly puts those fears to rest.

**Notes for the Chapter:**

> This is so very long overdue, and I apologize. There is still no solid deadline for the rest of the chapters, but I will post them as soon as the writers finish them. In the meantime, I do hope you enjoy this chapter! Josiah is quite fond of the potential member.
> 
> This chapter was written by myself. My tumblr is @morlawny. <3

You could feel the toll that all of this was taking on your body as you were gently set down on one of the cots in the medical tent. A soft sigh left your lips as you pulled the thin robe tighter around your body, and thanked the one who had graciously brought you here to recover. They gave you a polite nod before excusing themselves and ducking out of the tent, no doubt to go find the next person who would be welcoming you to the gang.

Your eyes slipped closed as you decided to take a quick moment to recuperate, mentally preparing yourself for the next person. They hadn’t told you who it was, but there were only a few people that you could think of, considering most of the gang had already had their turns with you. Whoever it was, you just hoped they were clean and not rough with you.

It felt like hours had passed when you heard the tent flap open again, letting in a cool breeze that made your skin prickle with goosebumps. Instinct caused your body to shoot up defensively; if you had your knife, you’d be clutching it tightly in your hand, ready to attack. The person who walked in stopped at your reaction, holding his hands up in surrender. His voice was gentle as he spoke, and you felt yourself relax slightly at his words.

“Easy, dear girl. I can assure you I’m not here to hurt you.”

Trelawny. Your eyes met his and you smiled apologetically, moving to sit with your legs crossed. You didn’t know Josiah that well, but what you did know, you certainly liked. He was charismatic and charming, and very easy on the eyes. He was also a drifter, but Dutch always welcomed him back with open arms. Arthur said it was because he always came back with good leads from his various connections all over the states. You figured that as long as Dutch and the others trusted him, that was enough for you, too. 

“Sorry, Josiah. Just startled me, is all,” you replied with a soft sigh, running a hand loosely through your hair. He looked sheepish as he spoke.

“It was my fault entirely, Miss (Y/L/N). I should have made my presence known before entering.”

You gave him a look when he called you by your last name, amused at how formal he was being. “You can call me (Y/N), you know. I don’t mind,” you told him. His expression turned to mock offense, and he reached up to cover his heart dramatically. 

“It’s only  _ polite _ , dear girl,” he said, coupling his words with a wink.

He moved closer to you, removing his hat and placing it on the wooden box next to the cot. You pat the space next to you politely and smiled when you noticed the soft blush flushing his cheeks. 

“Nervous?” you questioned, causing a light chuckle to escape him.

“Not at all, darling. Though, I could be asking you the same thing,” he quipped in response, his eyes glinting in amusement. You felt yourself blush at the words, and your eyes fell to your lap as you tried to hide it. Josiah was very observant, however, and reached forward to tilt your chin up with his gloved fingertips, his expression curious as he studied yours. 

His eyes were certainly a beautiful color, you noticed. A stunning mixture of green and brown; soft, but just piercing enough to stop you in your tracks. Your blush deepened as his expression turned into something… different; something that caused heat to pool low and deep in your abdomen. His next words were soft as he spoke again, his eyes locked with yours.

“Do you feel well enough for this?”

It was certainly polite of him to ask instead of taking what he wanted… The same couldn’t be said for a few other men in camp.

You gave a silent nod, lips curving into a small smile of appreciation. Josiah returned it, and began his work.

Long, slender fingers took gentle hold of the hem of your robe, and moved it aside, exposing the soft skin underneath. The heat in your abdomen spread further now, causing most of your skin to turn warm under the man's touch. Something about this felt… taboo, in a way, like what you two were doing was wrong. Then, it hit you. 

You briefly remembered Arthur mentioning Josiah's wife and children in passing, something about accidentally finding the man's home in Saint Denis. You weren’t sure if the man’s wife knew about his secret, about his second life, but you couldn’t help but feel a little guilty about what you two were doing.

His lips were in the juncture of your neck and shoulder now, warm and surprisingly soft, combined with the gentle scratch of his infamous mustache. Your eyelids fluttered closed at the feeling, and you couldn’t help but bare your neck to him as instinct took over. He quickly took advantage of this and kissed up your shoulder and to your neck, sliding his fingers through your hair as he did. 

You released a soft breath as you felt his teeth gently graze the soft skin, and suddenly, you were being moved. Clothing fabric brushed against your bare legs and when you opened your eyes, you looked straight into Josiah’s. He’d moved you to his lap, adjusting your legs so that you straddled him. His eyes never left yours as his gloved fingers made their way up your thighs, making your entire body shudder with anticipation.

Josiah’s hands felt perfect against your skin. You could tell he was good with them, and he hadn’t even given you a chance to prove it, yet. Another breath escaped you as you felt his erection starting to press against the underside of your thigh, and you couldn’t stop the blush that flushed your cheeks again. Even clothed, you could feel that he was well endowed. A knowing smirk made its way onto his face and you narrowed your eyes at him, trying to act irritated at his smugness; in reality, it turned you on more than you’d like to admit.

“You might reconsider that look on your face, (Y/N), it might just freeze that way,” he joked, earning an eye-roll from you. The irritation quickly vanished, however, when one of his gloved hands reached up to hover in front of your mouth. His eyes locked with yours as he spoke, his tone causing your entire body to shudder.

“Remove it, darling.”

A soft breath escaped you as you realized what he wanted you to do, but you gladly obliged, taking the tip of the white fabric in your teeth and pulling your head up, keeping eye contact with him all the while. You felt his erection twitch eagerly against your thigh, and the hand that was holding it was squeezing it just right. The heat in your abdomen was searing, now, and all you could think about was Josiah filling you up so  _ perfectly _ .

The glove slipped off of his hand after a moment, and once it did, his bare fingers found their way back to your thigh, slowly, teasingly making their way toward the heat between your legs. Your heart raced wildly in your chest as your gaze held his, and you had only realized you were holding your breath when his finger rubbed the middle of your entrance, sliding halfway between the folds and making you gasp softly and drop the glove. He knew what he was doing, and you weren’t sure whether to be anxious or eager. All you knew was that you wanted more, and if you gathered anything from this, you were sure Josiah would gladly oblige.

Without warning, his finger pushed further inside, rubbing right against the sensitive bundle of nerves just past the entrance. Another gasp escaped you and you gripped both of his shoulders as a reaction, squeezing hard as he continued to rub his finger against it. It wasn’t often that men knew where this spot was, but Josiah seemed to know exactly where to go. It made you wonder exactly  _ how _ experienced he was.

His piercing gaze never left yours as he continued to finger you, and you felt yourself blush as you realized the kind of faces you were making in response to his assault. You probably looked like a fool, but if he thought so as well, he certainly didn’t show it. In fact, it looked like quite the opposite. It was clear that he enjoyed what he was doing and how you reacted to it, but all your mind could fathom right now is how badly you wanted him inside you.

You made that thought clear as you reached down with one hand, keeping yourself anchored with the other on his shoulder, and palmed his cock through his trousers, eliciting a sharp inhale from him. The hand on your hip tightened, and you gave him a smirk, continuing to tease him by grinding your entrance against his very obvious bulge.

In one swift movement, one you nearly missed he was so quick, he'd unbuttoned his trousers and tugged them down a bit, along with his underwear. The garments stopped at the middle of his thighs, and you couldn’t stop the quick breath that you exhaled as you took in the sight of him. Before you could do anything, he quickly pulled you down by your shoulder so that your ear was next to his lips.

“Why don’t you take a ride, dear girl?” he murmured, squeezing your thigh and causing your entire body to shiver with delight. The man certainly knew how to make you want him, and you were more than willing to oblige.

  
“With pleasure, mister Trelawny,” you responded in a sultry tone. You braced yourself by holding his shoulders, lifting your hips and taking position over him. Careful not to break eye contact, you slowly pressed your slick entrance to the tip of his erection, letting out a soft breath as the hard flesh began to enter you.

You watched his face as you continued lowering yourself onto him, taking in each small reaction that he made as his girth stretched you open. He did the same, tightening his grip on your hips as your jaw dropped from the feeling. It didn’t take long for him to fill you up, but once your hips were flush against him, his expression darkened; turning more lustful than before. You felt fit to burst with his cock inside of you, but  _ God _ , did it feel good.

You started to test the waters, lifting your hips so his cock slid down inside of you, leaving you feeling surprisingly empty. A soft breath escaped you as you thrust your hips down, taking all of him inside of you once more.

Josiah’s head fell back in response, accompanied by a light gasp, but only for a moment. He quickly regained his composure. You, on the other hand, were far from composed. Your mouth hung open as he began a steady rhythm, not taking his eyes off of yours as he continued his thrusts. 

It was all you could do not to cry out in pleasure; perhaps that was what he wanted you to do. The look in his eyes was dark, primal... something you hadn’t ever noticed before when making love. You were sure that if this were any other time, Josiah wouldn’t be holding back as much as he was right now.

His fingers had a near bruising hold on your hips as he continued pumping into you, letting out small, breathy moans as parts of you rubbed him  _ just  _ the right way. You took a moment to regard him, taking in his uncharacteristically disheveled appearance with a soft breath of your own.  _ Surely he realized how sexy he was like this _ .

You made it a point to thread your fingers through his dark curls as you rode his cock, not taking your eyes off of his as you could feel your orgasm nearing closer and closer. By the look on Josiah’s face, he was getting closer as well. The man leaned into your touch, keeping his iron grip on your hips.

“Josiah,” you breathed, gasping softly as his cock hit the bundle of nerves once again. That was it; you had lost the little control you had. Your body jerked and trembled as your orgasm ripped through your body, and that, along with the way you tightened around his cock, was enough for Josiah.

He quickly removed himself from your warmth and positioned his cock between you both, pumping it just once before he released with a moan. His jaw hung momentarily as he rode his high, and you couldn’t help but notice how spectacular he looked like this. Both of you took this quiet moment to revel in the act that had just taken place and regain your composure.

You began to move off of him back onto the bed, wincing slightly as you stretched your legs from their folded positions and laid on your back. You hadn’t been in that kind of position for quite a while, and it showed. You felt movement beside you and turned your head to look right into Josiah’s eyes, which were accompanied by a small smile.

“Mind if I lay with you for a while?” he asked while folding his hands loosely over his chest.

You smiled back and gave a small, almost sheepish shake of your head. He’d just given you probably one of the best fucks you’d ever had, and you were still acting like a shy school-girl around him.

“Marvelous.”

He shifted his torso so it dug a little deeper into the cot, and turned to face you, draping his arm lightly across your waist. You took this opportunity to move a little closer as well, reveling in the warmth that his body emitted. It was especially nice considering the chilly night outside the tent. He leaned over you to blow the flame from the oil lamp, then settled himself back beside you again.

It wasn’t long before you heard his soft, slow breathing, indicating that he was now asleep. You smiled again, and let yourself relax a little more, soon falling into a light slumber yourself.


End file.
